


The First Time (Sister/Daughter!cest Winchester) Mini Series

by neganslucilletblr



Category: Supernatural
Genre: Angst, Brother/Brother Incest, Brother/Sister Incest, Daughter!Reader - Freeform, F/M, Father/Daughter Incest, Fingering, First Time, Fluff, Gay Sex, Loss of Virginity, M/M, Multi, Oral Sex, Orgasms, Sex, Sister!Reader, Smut, Threesome, Wincest - Freeform, blowjob, dark themes, dub-con, handjob, inappropriate relationship, m/m - Freeform, virgin!reader
Language: English
Status: Completed
Published: 2020-09-13
Updated: 2020-12-03
Packaged: 2021-03-06 15:34:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 19,992
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26441287
Author URL: https://archiveofourown.org/users/neganslucilletblr/pseuds/neganslucilletblr
Summary: Y/N is ready to become a woman and lose her virginity, but the three men in her life are too protective to let it be just anyone. They are determined to give her the best first time possible - even if it means with them.
Relationships: Dean Winchester & You, Dean Winchester/Sam Winchester, John Winchester & You, Sam Winchester & You
Comments: 15
Kudos: 155





	1. Part One

**Author's Note:**

> This is a commission for one of my All-the-Way Patrons. Parts to come out once a month.
> 
> Part Tags: kissing, angst, controlling, arguments, fem masturbation, incestuous thoughts

His hand started to slowly make its way from your waist to your breast as he squeezed gently. Your breathing caught in your throat as you felt him grope you over your shirt. Your kiss became a little more hesitant as your breathing grew heavier against his lips and your heart beat started to thud so hard, you were sure he'd feel it from where his hand was. 

“Wanna take this to the back seat?” he asked quietly. You glanced over to the place in question and swallowed. 

“Ye-yeah okay,” you nodded, agreeing. You watched him climb out of the car and took a deep breath before getting out yourself, straightening up your skirt and getting in the back of the car where he was waiting for you. 

“C'mere, baby,” he prompted. You slid in alongside him, closing the door behind you and he kissed you again, pulling you closer to hold your body against his. His hand landed on your bare thigh and started to move upwards, just under the hem of your skirt.

“Wait, Evan,” you stammered, putting your hand over his. 

“Yeah?” he prompted, pulling back. 

“We urr- we're not gonna... You don't want to do it here, right?” you pressed nervously. 

Evan glanced around the fairly empty school parking lot. 

“You don't want to?” he asked. “Thought we talked about this, thought you said you were ready.”

“Yeah, yeah I am... I just... I don't know, thought it would be in a bed, not... here,” you concluded, blushing. A small frown tugged on his brow for a second but he licked his lips and nodded his head. 

“Yeah, of course baby. No, you're right. It needs to be special. Why don't you come to my place this weekend whilst my folks are away? I'll make it special, I promise,” he smiled. You bit your lip and nodded your head in agreement. 

"Yeah, that sounds good."

“Great. Well, until then, doesn't mean we can't have other fun,” he smirked, kissing you again. 

You were a little more relaxed now, knowing it wasn't going that far, even though you'd never even been to second or third base before either. You let him lay you back on the leather seat, and his hand once more returned to your thigh and started to make its way up the inside of it, under your skirt higher and higher, as you felt the arousal start to pool between your legs. Evan was pulled off of you abruptly as you heard the car door swing open. The car door on your side also flew open and you realised Evan was being dragged out of the car, and the second you caught a glimpse of that brown leather jacket you scowled. 

“Dean!” you shouted out when he roughly grabbed the scruff of Evan's shirt. You felt hands wrap around your arms and yank you out of the car yourself. As you got to your feet you turned to glare at your younger older brother, Sam. “Get off me,” you grumbled, shrugging him loose. “Dean, stop! Please!” You begged, looking back to see Dean towering over Evan, glaring down at him. “Dean!” 

“You touch my baby sister again, you so much as lay a fucking finger on her... you are not gonna want to see how bad I could make it for you, you got that?” Dean growled. Evan merely nodded, and Dean ripped open the driver's door and shoved Evan forward. “Get the fuck out of here.” Evan scrambled to get into the car and start the engine, before pulling away with the tyres squealing. 

“You're fucking assholes, both of you,” you grunted, glaring at them both. Sam scoffed to himself and Dean's angry eyes suddenly honed in on you. “What are you even doing here? I told you I was getting a ride back to the motel,” you crossed your arms over your chest. 

“Yeah and you should've been back an hour ago. Good job I came looking,” Dean snapped, shoving his way past you and purposefully knocking your shoulder as he went. 

“You're so controlling! You're just like Dad!” you shouted after him. Dean turned back around and towered over you, glaring down at you with narrowed eyes. 

“Do you know what kind of girl fucks a jock in the back of his car? Sluts. Are you a slut, sweetheart? That the reputation that you want following you around?”

“We weren't going to fuck,” you argued.

“Not what it looked like to me. Looked like you were letting him have a good feel,” Dean retorted. 

“This is my body, Dean, I can let whoever I want touch it, it's not your business.”

“You're my baby sister, of course it's my business.”

“No it isn't!” You looked at Sam for some back up, but considering he'd just helped Dean on his _rescue_ mission, you figured he wasn't going to be much help to you now. Dean stormed over the Impala and opened the back door.

“Get in,” he growled. 

“I don't wanna go back with you,” you told him adamantly, crossing your arms over your chest. 

“Don't make me fucking put you in there, Y/N,” Dean warned. You glanced at Sam one last time, but he was just staring at you, waiting for you to obey orders, like the good little soldier your father raised you all to be. 

You reluctantly climbed into the back and flinched a little when Dean slammed the door closed behind you. Both your brothers slid into the front of the car, and Dean pulled off, heading back towards the motel. 

“It's humiliating,” you told them both. “No guy wants to date me because you two scare them off. I thought it would be better when Sam left last year, but you're still just showing up and embarrassing me.”

“Good, no guy should be dating you or touching you, and he certainly shouldn't be fucking you.” 

“Why not?”

“You're too young for that,” Dean argued. 

“You know I'm eighteen, right? I turned eighteen a month ago,” you reminded him. “How old is acceptable to you?”

“Preferably never.” 

You rolled your eyes, crossing your arms over your chest stubbornly. 

“You're both fucking hypocrites,” you argued. Dean glanced into the rear view mirror to glare at you, and Sam shot a glare back over his shoulder. “You think I didn't hear about you hooking up with girls in the supply closets in school? You think I didn't know what you were off doing when you'd dump me at a diner for an hour. You think I can't hear you in the next motel room when Dad goes on a hunt overnight?” you asked them both. The brothers shared a look but didn't reply. “It's embarrassing that I'm eighteen and still a virgin,” you complained with a blush. Dean glanced back at you again and suddenly his eyes fixed back on the road. 

“Nothing to be embarrassed about,” he offered. You scoffed and rolled your eyes. 

“I'm never gonna get laid if you two keep treating me like a baby,” you argued quietly. 

“We're just looking out for you, protecting you,” Dean explained. 

You grit your teeth and drew a deep breath. 

“Don't you realise how fucked up it is that I've been shooting a gun since I was ten years told, I've been on hunts and killed monsters, and I can fight with a knife better than both of you put together, but you're scared about me having sex?” Sam glanced back at you this time. 

“That's different,” he spoke up, weakly jumping to their defence. 

“Why? Because Dad said it was okay?” you pressed. “Because we were raised to fight?” Silence. “Everyone in school is having sex,” you complained. 

“No, everyone is saying their having sex,” Sam argued. “Just because some jock wants to fuck you, it doesn't mean you should do it.”

“God, neither of you are listening to me! I want to have sex,” you shouted loudly and clearly. “Evan isn't like that, okay? He's a nice guy and we've talked it through, and we'll be sensible, I promise.” The boys glanced at each other again. 

“You're the reason there are condoms missing from my bag, aren't you?” Dean grunted. 

You blushed violently and looked down to your lap. 

“Like I said, I'm being sensible.”

“Jesus Christ,” Dean grunted. 

“Told you it wasn't me,” Sam told Dean with a shrug. Dean glared at Sam then turned back to the road. 

“You don't get to do this, you're not in charge of me, I'm an adult,” you told them adamantly. “Sex isn't this dirty secret, it's natural and it's totally normal for me to want to do it, you know.”

“Okay,” Dean nodded. You frowned, not sure what you'd said to win the fight so easily. Was he really just giving in like that? Maybe his issue was the whole protection thing, and now he knew you had that covered then he was fine with it? You almost scoffed to yourself, of course Dean wasn't fine with it. Something was going on. 

“Dean,” Sam argued. 

“No, Sammy. She's got a point. She's eighteen, she can fuck who she wants. Not our call,” Dean told him. “You know, Y/N, I think you're right. It is totally normal and natural. In fact, why don't me and Sam talk you through it, you know, make sure you're prepared. Nothing to be embarrassed about right?” 

“No, you're okay,” you grimaced. Your brothers were the last two people you should be talking to about sex. 

“No, I think as me and Sam are guys, it'd be good to hear it from our point of view, right Sammy?” Dean prompted. Sam remained quiet, clearly also at a loss as to what game Dean was playing. “Have you ever given head before?” Dean asked casually.

“Dean!” you complained, your cheeks burning. 

“Has a guy ever fingered you? Have you ever even touched a real dick?” Dean went on. 

“Stop, Dean,” you whined. 

“Dude,” Sam also complained.

“If you can't talk about it, how are you supposed to do it, huh?” Dean pressed. 

“That's different, you're my brother, it's – it's wrong,” you argued. 

“Me and Sammy talk about sex,” Dean told you casually. 

“You're both guys, it's different.” 

Your cheeks were still burning with humiliation at Dean's comments. Dean kept glancing back at you through the rear view mirror, and as the conversation died he started to hum along to the music. 

“Don't tell Dad,” you asked weakly. “Please don't tell Dad,” you begged. 

“What's the matter, sweetheart? Afraid our old man will have something to say about it?” Dean smirked. 

“You know he will. Dean please, I could be thirty and he'd have an issue with me having sex, I'm his little girl,” you argued. Dean didn't confirm or deny that he wasn't going to tell John, which made you a little uneasy. 

“I was fifteen,” he finally said. “Her name was Hayley Allbank.” You crinkled your nose, realising what he was telling you. “Fucked her behind a Dennys.”

“Dude!” Sam complained, a slight laugh in his voice. 

“I almost shit myself. I thought I was just getting head, but she wanted the whole nine yards,” Dean continued. You hid your face in your hands. “She pulled out the condom and I had to have a serious mental pep talk with myself.” Sam was trying not to laugh as he continued to shake his head at Dean's story. “Pretty sure I lasted like a minute, tops,” he added. “My point is, first times are awful and messy,” he spoke louder, as if addressing you personally. “How was yours, Sammy?”

“Dude, I'm not -” Sam stopped himself mid sentence and shook his head. 

“C'mon, I told you mine. This is a bonding moment,” Dean encouraged. You wanted to die, you wanted the seemingly never-ending car journey to be over. But you didn't know what was worse, the fact you were embarrassed to be hearing such intimate details about your own brother or the fact that you were jealous. You were fairly sure, however, that the jealousy you were feeling was because they had stories to tell and you didn't. 

“I was sixteen,” Sam begrudgingly said, clearing his throat. “We urr- I went to hers to study.”

“Bet you studied something, huh Sammy?” Dean joked, jabbing Sam in the side as he laughed. Sam blushed, you could see the tips of his ears turning pink. 

“It was fine,” he concluded. 

“You know, you're not doing a very good job at arguing your point. You were both younger than I am now, and you both did it with random girls. Dean, you did it behind a Dennys,” you pointed out. “At least me and Evan are dating and we like each other and we've planned it to be special.” Dean scoffed.

“No such thing, sweetheart.” You rolled your eyes again. 

“Only because you've never had a proper girlfriend.”

“I have,” Dean frowned. 

“I mean a girl you've not just fucked more than once. That doesn't count, Dean. I mean actually had feelings for.” Dean remained quiet. “If you ask me, you're just jealous that my first time might actually be meaningful.” You pulled up into the motel parking lot and Dean slammed on the brakes. His mood that had seemed to be lifting had dropped dramatically again, and you sighed as you grabbed your school bag and climbed out of the car. 

Dean let you into the room and you found your father huddled over some newspaper at the dining table. 

“Where have you three been?” he grunted. He looked up and glared at Dean in particular. Dean was always the one that got in trouble where the three of you were concerned. 

“Picking Y/N up from school.”

“School ended two hours ago,” John snapped. Dean glared at you before turning back to John. _Oh fuck_. 

“I had to pull some guy off of Y/N,” Dean explained, a tone of smugness to his voice because he knew he was landing you in trouble. Your fathers' eyes darted to you as they narrowed. 

“What?” he pressed. 

“Sonofabitch had his hand up her skirt and everything.”

“Dean!” You shouted. “Daddy, it wasn't – he's my boyfriend,” you argued weakly. John's jaw clenched. 

“Oh, it gets better, Dad,” Dean smirked over at you. “Reckons she's gonna let him pop her cherry.” Your cheeks flamed red and you would've killed Dean right there and then if you thought you'd get away with it. “You're the one that said that sex is natural and normal. So we should talk about it right? Be open and honest?” 

“Fuck you,” you grunted. 

“Y/N,” John growled. You slowly looked back to your father and felt your cheeks burn even hotter. 

“Daddy, I'm eighteen,” you argued weakly. The way he was looking at you didn't make you feel all that confident, even though you were trying to be. 

“I don't fucking care, if you think I'm gonna let some boy put his hands on you,” John grunted. You drew a deep breath, hating how possessive and controlling the three men in your life were. You were never going to lose your virginity at this rate, between them they'd make sure of it. 

“He's not just some boy, he's my boyfriend,” you retorted. 

“I don't care who the fuck he is, he's not good enough for you.” You rolled your eyes. 

“No guy is ever gonna be good enough for me, is he? Not unless he's Dean or Sam.” John glanced at the brothers. 

“At least I know I could trust them to never hurt you, or take advantage of you.”

“Yeah well, news flash, they're my brothers, I can't have sex with them.” You knew better than to sass him back, or so you thought, but the words were out of your mouth before you thought of the consequences. 

“I'd rather that than some boy we don't know. What have I taught you about trusting people, Y/N?” You couldn't believe your father was even saying what he was saying. He'd rather you fuck your own brothers because of his extreme trust issues? You glanced at Dean and Sam, sure they'd be just as horrified as you, but they weren't. They were both glaring at you like you were the one in the wrong still. 

John let the silence grow. 

“You're not letting that boy - or any boy for that matter – touch you again, Y/N, you hear me? Me and your brothers are the only men in your life you can ever trust.” You crossed your arms over your chest, but didn't answer back this time, deciding you'd pushed your luck enough for one day. “I've gotta go out, boys don't let her leave your sight.” John grabbed his coat from the back of the chair and left, slamming the door closed behind him.

“You son of a bitch,” you glared at Dean the second the door was closed. “Why did you tell him?!” Dean chuckled quietly. 

“I'm sorry, okay, sweetheart?” he asked, stepping closer. “We just don't want you to regret your decisions. You can only give it up once, it should be to someone special.” 

“Evan is special to me,” you argued weakly. 

“You've known the guy a month and this time next month we'll be out of here,” Dean reasoned. 

“Well I guess Dad's right then, you three are the only men I could trust, you're the only three that are gonna stick around, right?” You were hoping that the sarcasm in your voice would highlight how messed up the statement was, but Dean smirked softly and gripped your chin. 

“Maybe it's not such a bad idea, you know.” 

He let your chin go and joined Sam on the couch as they watched some b-rated horror movie. You stared at the back of their heads. They were winding you up, they had to be. None of them were serious about you actually losing your virginity to your own family. They were just trying to put you off, right? You walked over to your bag and grabbed some spare clothes, deciding to take a shower. You locked yourself in the bathroom, shutting out the noise of the TV as you started to run the water and stripped as it warmed up. Stepping under the stream once it was hot enough, you began washing. You'd be lying if you said you didn't want to find a guy that was a mixture of your father and brothers. You wanted a guy as smart and caring as Sam, you wanted a guy as protective and loyal as Dean and you wanted a guy as hard working and strong willed as your father. It was a love hate relationship that you had with your family's controlling tenancies. You knew they just wanted to keep you safe and make sure you didn't get hurt. You were the baby of the family, and the only girl, the three of them treated you like you were made of glass a lot of the time. 

Dad had never even given you _the talk._ In fact, the only reason you found out about sex was because you'd walked into the wrong motel room one day when you were younger, and saw John with some woman. You'd ran back to your brothers in the next room, and between them they'd stumbled through an awkward explaination about sex and what happened during it. Sam was as wide eyed as you were when Dean gave up and decided to show you porn instead. That was an uncomfortable twenty minutes for everyone. Especially with all the questions you'd followed up with. But like with everything when you were growing up, Dean had done his best to step up where your father didn't, and between the three of them, they really hadn't done a bad job. You did feel loved and safe with them. 

But you still felt increasingly frustrated that they were being such major cock blocks. You just wanted to get all the first times out of the way. You just wanted to experience it for yourself. You were sick of the daily showers, the only privacy you had to touch yourself. You were sick of wondering what it all felt like. You just wanted to know, you wanted to join in with the conversations your friends would have. It was all so embarrassing. You were so sexually tense, it would even affect you when you'd see Sam or Dean shirtless, or when you'd share a bed with one of them and you'd wake up touching, or their legs wrapped with yours, or their arms flung over you. You found yourself touching yourself when you could hear Dean trying to fuck a girl silently in the bathroom when he thought you and Sam were asleep. All that stuff shouldn't turn you on. Thinking about your brothers shouldn't turn you on. 

Even thinking about being turned on was turning you on. You sighed heavily to yourself and rubbed a hand down your front to between your legs. You started to rub at your clit softly, biting back any whimpers or moans that were threatening to bleed through your lips, knowing Sam and Dean were still very much awake and only the other side of the door. You thought about Evan touching your breast in the car earlier on, how his hand snaked up your skirt, and you imagined you weren't interrupted, what he'd have done to you on that back seat. You imagined your back pressed to the leather seat as he fingered you, you imagined the moans and groans he'd pull from you with his mouth as you looked down your body to between your legs and he'd lift his head to smirk and - Dean. Dean's green eyes stared back at you in your mind's eye, between your legs, plump lips swollen and shiny with your slick, and you shouldn't, but in your mind you push his head back down and you let him carry on because you were so fucking close to -

“Y/N, hurry up,” Dean called, thumping on the door. You gasped for breath, so close to coming undone as the image of him between your legs faded. “I can't wait,” he told you, and you heard the door open. You were so close you couldn't even make your fingers stop rubbing in circles over your clit, the shower curtain the only thing stopping Dean from seeing you touching yourself like this. And you should've been yelling at him to get out – he was probably expecting it, but you couldn’t speak without moaning. You assumed he was peeing, but couldn't hear it over the shower, and then you heard the jangle of his belt and his fly and you imagined him stood the other side of that nasty, paper thin motel shower curtain, his cock in his hands and you wondered if it's long or thick or both. The coil snapped and your knees almost buckled as you screamed silently and squeezed your eyes closed. You heard the flush sound and the water turned freezing. It was just what you needed to snap your body back into action, as you jumped out of the spray.

“Son of a bitch, Dean!” You screamed, realising you'd stepped beyond the curtain's cover, and Dean stared at you naked and dripping wet for several seconds. His lips parted slightly and his green eyes dared to drag over your body. “Grab me a towel, asshole,” you grunted after a few moments of feeling the intoxicating mix of arousal and shame flood over you. You'd just got off thinking about your brother's cock and now he was looking at you naked, and part of you - a fucked up, twisted part of you - was hoping he'd slam you against that shower wall and show you just what he could do with the thing between his legs. Dean finally snapped into action and grabbed the towel on the rail, handing it to you before leaving the bathroom quickly. Your heart was racing as you covered yourself up and stepped out of the tub. Jesus, this was so fucked up. And this was exactly why you needed to get laid. To stop these weird fucking thoughts. 

You needed to compose yourself before stepping out of the bathroom and facing Dean again, and dressing slowly allowed you to do that. You suddenly felt very self conscious in the large shirt of Sammy's you'd stolen once and never given back, as you headed straight for bed without even looking at your brothers. But they were looking at you, you could feel the burn of their stares as you passed them. 

“Gonna get pizza, want some?” Sam asked. 

“No, I'm going to bed,” you told them.

“Bed? It's not even seven,” Dean scoffed. 

“I'm tired, long day,” you lied, faking a yawn. 

You climbed into bed and turned your back on them, staring at the wall. You'd lied, you were nowhere near tired, and you lay there wide awake, staring at the shitty blue wallpaper and listening to whatever crap your brothers were watching, whilst thinking about what the fuck you'd just gotten yourself off to, until it grew dark and you heard the boys talking about heading to bed themselves. You heard movement behind you and felt the covers being thrown back, the mattress dipping as someone climbed in. _Not Dean, not Dean, not Dean._ It was Dean. His aftershave was unmissable. Given the fact your father would be gone most, if not all night, Sam taking the spare bed made the most sense. Sam and John rarely shared beds, so you often slept with Sam. So when John was away, Sam would get the privilege of the empty bed; something you'd never been given the courtesy of. 

As Dean settled behind you, you felt his foot push between your ankles and your heart beat sped up again. You could sense from his body heat he was only in his boxer shorts, and if you were going to sleep before, you definitely weren't now.


	2. Part Two

**Notes for the Chapter:**

> Part Tags: sex dream, talk of loss of virginity, incest, brother/sister, dry humping, fingering, handjob, angst, mentions of wincest, mentions of m/m

_You couldn’t believe it was finally happening. Your heart was thudding in your chest as you swallowed hard and watched as he stripped off his boxers at the foot of the bed, before climbing onto it, crawling towards you. He kissed the nerves away in your stomach, and you tried to relax a little more into the kiss. You’d read that it hurt less if you were relaxed, and you knew you’d never experienced anything like him inside you before, so you definitely needed this to go as painlessly as possible._

“ _It’s gonna feel so good, sweetheart, gonna take real good care of you,” he purred, encouraging you to lay down beneath him. You whimpered, nodding your head as you bit your bottom lip. “I can already see how wet you are for me, so just relax, I’ve got you.” You drew a deep breath and stared up at the ceiling, chewing your bottom lip anxiously as you felt his hands smooth up your thighs whilst gently prying them open wider. You obliged, his eyes sparkling up at you as he looked to judge your reaction._

“ _Oh god, please,” you begged. Why was he dragging this out? You wanted this more than anything, and the longer he was taking the more nervous you felt and the less relaxed you became._

“ _Patience baby, this only happens once,” he purred._

“ _Dean, c’mon please,” you pleaded. Dean chuckled lowly, his hand reaching your centre as his thumb pressed gently over your clit. And then he was Sam, his long brunette hair getting in his eyes a little as he flicked it away and his free hand fisted his cock._

“ _Sammy, please,” you begged, reaching for his wrist to pry his hand away._

“ _Wait, Y/N,” he told you gently. “So impatient.” Dean again, his low drawl washing over you, making your body jolt._

“ _Just fuck me, please Dean,” you begged louder. Sammy again, then Dean, then Sam. You were growing increasingly frustrated. Then John._

  
  


“ _No one gets to touch my baby girl, I don’t trust any other men,” he told you quietly, his fingers teasing around your opening._

“ _No, Daddy, only you, I promise,” you whimpered, bucking your hand up into his touch._

“ _There’s my girl,” he cooed, “all ours.”_

“ _Yes, yes Daddy, all yours. Please, I need it I need-” Your words died in your mouth, he was Dean again. Fuck. “Dean, please,” you begged._

_Dean looked up at you and nodded, “okay baby, okay.” You let out a breath of relief and watched as Dean leaned over you, looking down your bodies as he grabbed his cock._

  
  


You startled awake to the feeling of pressure between your legs, realising that you’d been dreaming. There was a leg shoved between yours as you lay on your side, and a hand lazily placed on your hip. You realised your hips had been grinding back unintentionally, and stopped yourself as you glanced over your shoulder nervously and saw Dean with his eyes still closed directly behind you. As you shifted a little to get away, Dean’s hand gripped your hip tighter, stopping you from moving, and it very quickly became apparent to you that he was hard and it was nudging between your ass cheeks through his boxers and your panties. You pushed down the immediate arousal it made you feel, and reminded yourself that your dream was just that - a dream - and Dean was still very much your big brother and that kind of thing couldn’t happen with him. 

  
  


You ignored the ache as you once again tried to move away from him, Dean shuffled closer and started to softly grind his hips against you, only making matters worse. You bit your bottom lip and told yourself not to give in to that burning need to respond to the touch, your body almost defying you no matter what your mind said. Dean grumbled softly against the back of your neck, his fingers digging a little deeper into your hip. The first roll of your hips back to meet his touch was accidental, something you’d not consciously decided to do, but after discovering how good it felt, the second one was intentional. He was painfully hard, rubbing in just the right place every time your hips met. You closed your eyes and chased your dream again, at least trying to give yourself the half asleep excuse, but it was no use, you were wide awake, your panties soaking wet, and your heart beating a million miles an hour. 

  
  


Dean’s hand slowly slipped around your hip towards the base of your stomach, his fingers splayed out as he hummed quietly again, that aura of still being half asleep about him - maybe even fully asleep, his reactions to you completely instinctive. Maybe if he woke up and remembered who you were he’d be disgusted in himself, the way you know you should be in yourself. You know you shouldn’t be letting him do this, and you certainly shouldn’t be _wanting_ him to do this. You should be tearing his hand away. But then Dean started to grind harder against you, and all those reservations died in your mind. The way he was thrusting was shifting his hand further down your body without him needing to move it, closer and closer to your panties. You grumbled yourself now, as Dean’s fingers ghosted over your clit through your panties, unintentionally, you assumed, because they were limp. Until they weren’t, and he was pressing down against your bundle of nerves purposefully. 

  
  


Your heart was in your throat. No guy had ever touched you there, particularly not your brother. This was so wrong, you should’ve been jumping out of bed, waking Dean up so he’d stop what he was doing, because there was no way he was aware of this like you were. Dean started to rub up and down, in time to the thrusts as his cock continued to press against your opening, only held back by two thin pieces of material. Your hand gripped the bedsheet hard, until Dean was pulling his hand away from your core and reaching for yours, uncurling your fingers from the sheets and guiding it back, behind your body towards his. 

“Wanna feel it, sweetheart?” he asked, his voice almost silent as he spoke against the back of your neck. Your heart stopped and lodged in your throat. He was awake. He was as aware as you were exactly what was happening, and he wasn’t stopping. “Want to touch one?” he murmured. His voice was thick with sleep still, and gruff, and it made your core throb. You clenched your thighs, squeezing his cock that was still trapped between them and Dean chuckled ever so softly. “You do,” he confirmed, continuing to guide your hand back until he was pushing it inside his boxers. “It’s okay, it won’t hurt you, I’ll show you,” he soothed. “Let your big brother show you.” 

  
  


You were taken back to days in the forests as Dean taught you to shoot a gun whilst John was on a hunt, how he’d come up close behind you and curl his hand around yours over the gun, showing you how to aim better, how to grip in the right places. You remembered how he’d linger behind you, his hand resting on your hip as you took your shot and how you’d miss his body warmth when he stepped back. You’d always assumed it was just the comfort of your big brother that you loved, but maybe it wasn’t. Maybe it never had been. Maybe it had always been something more and you were too ashamed to admit it. 

  
  


Dean squeezed your hand softly, encouraging you to open it and then slowly guided it closer to his cock. His skin was hot and softer than you’d imagined it would be. Dean’s hand wrapped around yours which made you curl your fingers around him. He was heavy and _thick._ He murmured softly and began guiding your hand up and down his length, bucking his hips ever so slightly. He placed soft, barely there kisses along the back of your shoulder and neck. His hand left yours, and you continued on your own, as he reached across your body again and his fingers went back between your legs. He rubbed over your panties again, and you gasped for breath. 

“Sh, sh, don’t wake Sammy,” Dean hushed. You nodded your understanding, not trusting yourself to make any noise that wasn’t a moan or a whimper. 

  
  


Dean’s hand moved under your panties and found your dripping pussy again, and he pushed against your stomach to encourage you to lay flat on your back. Your hand twisted around his cock as you changed position, and you were almost too ashamed to look him in the eye but as soon as his green eyes locked onto yours, you couldn’t breathe. 

“Fuck baby, you’re so wet,” he whispered, barely audible. Biting your bottom lip you nodded. “Really do need some attention, don’t you?” he continued. You nodded again. Dean dropped his face into the crook of your neck, bringing his mouth to your ear. “So desperate, bet you’d let me fuck you, wouldn’t ya?” Your eyes rolled and you were utterly ashamed of the answer swimming around in your head. _Yes._ You wanted nothing more. Dean was bucking his hips against your hand, so you squeezed harder and worked a little faster, making him groan louder than he’d done before. He swallowed it quickly and glanced over his shoulder to Sam who had his back to you both. 

  
  


Dean slowly slipped a finger inside you, making you gasp. It was different, somehow, having someone else’s finger inside you. He curled it upwards and rubbed against the sweet spot you’d only recently found yourself. He was better at this than you, somehow. Your free hand gripped his wrist tightly, but he didn’t let that stop him as he slowly started to fuck you, pulling out to add a second finger. This felt better than you’d ever imagined it could, and it only made you more curious as to what his cock would feel like. It was so much thicker and longer than his fingers, and just the thought made you clench around him. 

“Wanted to feel you for a long time, Y/N,” Dean confessed, “I was jealous of that son of a bitch.” You swallowed hard and looked up at him, biting your bottom lip to suppress your moans. “Touching my baby sister. No other guy deserves this, deserves you,” Dean growled, fucking you harder and faster.

  
  


“Dean, Dean,” you chanted, and Dean hushed you again as Sam shuffled in the bed across from you. You swallowed hard, trying your best not to cum on his fingers. But Dean wasn’t letting you get away with it that easily. He curled his fingers and used his thumb to rub in circles over your clit. You couldn’t breathe, couldn’t move as your hand stopped working his length, and all you could focus on was the orgasm Dean - your older brother _Dean -_ was about to give you. 

“C’mon baby,” he encouraged quietly, thrusting his hips into your hand. You came around his fingers, clenching them hard as Dean slowed down and you felt your hand getting hot and sticky inside his boxers as he came too. “Fuck,” he gasped. “Been a while since I’ve cum in my pants, sweetheart,” he panted. 

  
  


Your alarm for school filled the quiet and you quickly jerked away from Dean, getting up and heading for the bathroom without even looking at either of your brothers. Your hands were shaking with nerves as you washed them clean of your brother’s cum, and your legs were shaking with the aftermath of your orgasm as your soaked panties clung to your skin uncomfortably. Why the _hell_ did you do that? You’d just got to second base for the first time in your life, with your own brother, after having some fucked up sex dream about both your brothers _and_ your father. You brushed your teeth to get the taste of regret out of your mouth, and heard the motel door open. Your father’s voice sounded out, asking where you were, and so you nervously stepped out into the room again to see Dean hunched over his bag, now dressed, and Sam was awake, but still in bed. 

  
  


“You’re going to be late for school,” John grunted. He was covered in blood, the hunt seemingly went well, and you nodded at him. You headed over to your bag and picked out some clothes. One of Dean’s tshirts had made it into your bag somehow, and normally you’d wear it to annoy him, but you weren’t feeling up to that today. You grabbed a change of clothes and headed back into the privacy of the bathroom. Once you were dressed, thankful to be in dry panties, you drew a deep breath and talked yourself up to stepping back into the room. The three of them were talking in hushed whispers, and you were petrified that Dean was disclosing what had just happened, and that John was about to kick off again. But Dean didn’t want anyone to know, right? He’d be just as ashamed as you, surely. 

  
  


When you returned, Sam was now also dressed. 

“Sammy, take Y/N to school,” John ordered, glancing at Dean. Oh fuck, he knew. Somehow he just _knew._

“Dad,” Sam protested, apparently he didn’t want to do that. 

“Give Sam the keys, Dean,” your father demanded. Dean rummaged in his pocket and dug the Impala keys out, throwing them at Sam who reluctantly caught them. “We’ll talk when you get back,” he told Sam, “I need to talk to Dean first.” Talk about what? Why were you feeling completely out of the loop now? You glanced between the three of them, but none of them were looking at you. Sam huffed and glanced in your direction before heading to the motel door. You took your cue to follow, grabbing your school bag. 

“See you later, sweetheart,” John smiled softly at you. You forced a smile to your lips as you passed him, and ignored Dean as you headed out. 

  
  


Sam was clearly in a bad mood as he slumped into the Impala and slammed his door closed. You climbed in alongside him quietly. You’d have rathered Dean take you, even after what had happened this morning, and that was saying something.

“You okay?” you pressed Sam gently. Sam glanced across at you as he started to drive you towards school.

“Fine,” he muttered.

“Was Dad’s hunt okay?” you asked, wondering if that’s what was going on.

“Yep,” Sam popped the ‘p’ and so you sighed, at a loss. You looked out of the window and watched the buildings pass you by.

  
  


“Are you mad about what happened yesterday?” you asked, afraid of the answer. Out of the three of them, Sam was the least controlling. He hated Dad’s iron clad fist rule as much as you did sometimes, but when it came to you, he always sided with John and Dean, and that irritated you.

“They’re right, Evan isn’t good enough for you.” You sighed heavily and rolled your eyes.

“Oh and the girl you studied with was good enough for you?” you taunted. Sam glanced across at you and his jaw clenched.

“That’s different,” he argued.

“Why because you’re a boy?”

“Yes.” You shook your head in disagreement.

  
  


“Look, sweetheart,” Sam sighed, “your first time with anyone is special, but it’s better when they mean something to you, trust me.” You looked across at him.

“Do you even remember her name because you’ve not mentioned it once,” you retorted with a scoff. Sam swallowed hard and drew a deep breath. 

“I’m - I’m not talking about Darcy,” Sam stammered out. 

“Then who are you talking about? You’ve got two firsts?” you laughed slightly, confused. 

“Kinda.” Sam let the silence grow, clearly not about to explain himself. Sam was only a year older than you, but it felt like he was years ahead when it came to experience. The boys and your father sheltered you, babied you, and you hated it. “I can’t explain it right now,” he added as you stared at him. “Dad is right for once, Y/N. You deserve better than all those boys.”

“That’s the problem, isn’t it, Sam? I’m never going to find a guy that lives up to any of your expectations, and that leaves me with two guys who are my brothers and one guy who’s my father, and that’s…wrong.” The truth in your words only served to hurt yourself as you remembered that morning.

“Maybe,” Sam agreed.

“ _Maybe?”_ you pressed. Sam reached across and grabbed your thigh, squeezing it for a moment and letting his thumb stroke back and forth. You looked down at his hand and felt the butterflies reawaken in your stomach. You found yourself hoping he’d slip his hand higher. Fuck, it was fucked up what you’d done with Dean that morning, but to be feeling like this about Sam too? There was something seriously wrong with you, there had to be. 

“I’d rather it be me or Dean or Dad than one of those jocks that are only gonna break your heart. At least I know we wouldn’t do that to you – _ever.”_ He gave your thigh one last squeeze before his hand slipped away, and you drew a deep breath. It was basically what your father had said the night before. How could they think like that and not feel grossed out?

“Still doesn’t change the fact you’re family,” you muttered. Sam glanced across at you again. You were getting to the school now. The same journey that had seemed to take forever the day before had seemed to have lasted seconds this morning.

“Didn’t seem to bother you this morning,” Sam noted casually as he pulled up outside the school. Your mouth suddenly went dry, and you stared at Sam wide eyed. He stopped the car and stared back at you, he looked bothered by what you’d done with Dean that morning - if that’s what he was referring to – but what else could he be referring to? And could you blame him for being bothered by it? God, you were in so much trouble now. You were positive John knew and now you knew Sam _definitely_ knew. You felt sick thinking about it. It should’ve never happened.

“Sam, I -”

“And it was good, right?” he pressed with a small smirk. Your cheeks were burning. “Dean’s good,” Sam nodded. Your mind was spinning as you were trying to figure out what Sam was saying. How the hell did you respond to that? And how did Sam know if Dean was _good_ or not?

  
  


“It was a mistake, it should never have happened, it was wrong and…” you swallowed hard, finally admitting it out loud.

“And yet you wanna do it again,” Sam finished for you.

“What? No, I… no, Sam,” you told him adamantly, not sure who you were trying to convince harder - you or him. 

“Okay. Have a good day at school.” Sam didn’t say anything else, and you got the hint, opening the car door. You turned back to say something but couldn’t find words. You were flustered as you got out of the car and closed the door behind you. As Sam drove off, he left you standing on the sidewalk, wondering what the hell just happened. 

  
  


_**Sam’s POV** _

Sam watched Y/N stood on the sidewalk through the rear view mirror and tightened his grip on the steering wheel. Despite getting himself off that morning to the sounds of her and Dean, whilst trying to still seem asleep, Sam was still wound up. Sam couldn’t deny he was jealous, of Dean or Y/N he wasn’t sure - maybe both. He always knew they’d have trouble with guys when it came to Y/N. He’d been in school with her for most of her life, only a year ahead of her, and he’d hear the way the boys would talk about her. But he’d always been there to scare them off before they could even get close. Now he wasn’t around and she already had some guy trying to get into her panties. Not that he could blame the guy. 

Sam’s mind wandered to what John could possibly want to speak to Dean about without him there, but then John had said that they’d talk when he got back, so maybe he’d find out. Maybe John somehow knew what went on between Dean and Y/N (he was observant like that), and wanted to separate them for a bit. Either way, Sam was speeding the whole way home to find out. 

  
  


But as Sam pulled up to the motel parking lot he noticed that John’s truck was gone. He frowned as he let himself back into the motel room to see Dean lazing back on the couch, watching some shit show on TV.

“Where’s Dad?” Sam asked, closing the door behind him slowly. Dean glanced over at him and then back at the TV. 

“Supply run,” Dean told him casually, his eyes back on the TV. 

“What did he wanna talk to you about?” Sam asked casually, trying to seem disinterested and like he was only making conversation. 

“What do you think?” Dean pressed. Sam licked his lips and drew a breath.  
“Don’t know, that’s why I asked,” he replied, feigning ignorance. Sam remained standing at the foot of the bed and he watched Dean turn the TV off before eloquently diving over the back of the couch to walk towards him. 

“C’mon, Sammy, let’s not play innocent,” Dean smirked, standing so close to Sam all he could smell was the unmistakable, distinct smell that was simply _Dean._ “Don’t act like you didn’t rub one out in bed next to me and Y/N this morning whilst I showed her second base.” The tip of Dean’s nose was practically nudging Sam’s as Dean looked down their bodies and his hand reached for Sam’s crotch. 

  
  


“Don’t,” Sam grunted, pushing Dean’s hand away. Dean looked up at Sam’s face and mockingly pouted. 

“Don’t be jealous, Sammy,” he cooed. Sam glared and backed away. “C’mon, I showed you the ropes back when, now it’s Y/N’s turn.” Sam drew a deep breath and turned his back on his brother. “Sammy, come on, man,” Dean prompted. “Who gave you your first hand job?” Sam’s jaw clenched, “blow job?” Dean added. Sam told himself to ignore Dean’s words. “What about the fact you were so worried about not being any good at fucking that Darcy girl, that I let you fuck me first?” 

“Exactly, Dean!” Sam shouted and turned around. “You were my first everything, and it meant something to me, I thought it was special… I thought _I_ was special.”

“Sammy, you’re my kid brother, of course you’re special. And Y/N is my baby sister. Don’t you want all her firsts to be special too?” Dean prompted. Sam glared. He didn’t like that what had happened between him and Dean wasn’t so special to just them anymore, but he also couldn’t deny that Y/N deserved what Dean had given him. “And we both know I’m a good teacher,” Dean boasted. 

“She’s not like us, man, she keeps saying that it’s wrong,” Sam argued. 

“It is wrong, Sammy, we’ve just never cared, and clearly Y/N doesn’t either, not after this morning.” Dean winked at Sam and it only made the jealousy stronger. 

“Why you, huh?” Sam shot out, realising what he’d said. What he’d _meant_ , as it dawned on him properly for the first time that maybe he wanted to be that person for Y/N too. 

  
  


“You wanna help me break in our baby sister?” Dean pressed with a deeper smirk than before. “Show her some tricks?” Sam gave a nonchalant shrug like the very idea wasn’t starting to make his cock harden. 

“Maybe,” he replied casually. 

“Nothing’s stopping you, man - I’m not stopping you,” Dean told him, holding his hands up. Dean stepped closer again, and this time Sam wasn’t so hostile. “You know, Sammy, Y/N has my lips… wonder if they feel as good as mine wrapped around your cock.” Dean’s hand went to Sam’s belt and Sam whimpered at the very thought, his cock growing harder still, but as Dean went to unbuckle the belt, the motel door opened and John walked in. 

  
  


Dean stepped back immediately and headed over to his bag as if he was looking for something, and Sam tried to shake off the flustered feeling he felt. John wasn’t an idiot, he knew full well what went on between the two of them, but he chose to ignore it, and the brothers chose to never bring it up. The only thing John had ever said on the matter was _Don’t let your sister catch you._ And so the brothers had been careful about that. It didn’t happen often between them, not now Dean could go drinking in bars with John, and Sam wasn’t in school anymore, sometimes able to use fake ID to join John and Dean, so they could pick up girls if they wanted to. Sam’s confidence with women had grown substantially over time as he got more and more experience under his belt, so Dean’s _lessons_ or _help_ wasn’t so much needed anymore. Though Sam would be lying to himself if he said that he thought that’s all they ever were. They weren’t. 

“You’re back,” John noted, placing the shopping bags down on the table. Sam looked between Dean and John, prompting John to say his piece. Dean had already let slip that this issue was to do with Y/N, and Sam wanted to hear whatever John had to say on the matter. John had never seemed particularly fazed about what his sons sometimes got up to when they were alone, but Y/N was his baby, he was more protective of her than Dean and Sam were, so maybe he’d have something to say about Dean touching his innocent little princess. “We need to talk about your sister,” John told them both. “Sit down.” Sam looked behind him and reluctantly sat on the edge of the motel bed, Dean sitting on the other as John stood between them and crossed his arms over his chest. 

  
  


“Y/N is eighteen, so I can’t say it surprised me that she’s suddenly interested in boys and sex,” John began, “I’m surprised she’s taken this long, in all honesty. Not after the way you two always think with your dicks.” Sam was about to argue that he wasn’t as bad as his brother, but then he remembered that he was jealous of his brother for fingering their sister because Sam wanted a piece of the action, and kept his mouth shut. “And we’ve never talked about it before, but I know you two had your own… _way_ of learning and discovering things,” John worded carefully. Sam felt his cheeks heat up and was sure Dean would be blushing too. “I’ve got enough bullshit to deal with right now to be worrying about that, you’re not hurting anybody,” John continued. “And, like I said yesterday, if Y/N is going to be doing that stuff - and she is whether we like it or not - I’d rather it be you.” 

  
  


Sam was shocked to hear John’s _approval_ about what Dean had done that morning, about what Sam wanted to do to her. Maybe he was getting too old to argue about it, maybe chasing down a demon for eighteen years was taking its toll, maybe he really was a shitty enough father to just not care. Either way, Sam was pleased to hear that John wasn’t going to be a problem. 

“But, I’m warning you now, boys,” John spoke up again, voice firmer. “You don’t get to fuck her,” he warned them, “yet,” he added. Sam frowned slightly and looked across at Dean, who looked just as confused. Then a smirk spread over Dean’s lips and he scoffed. 

“You want to be her first,” he laughed. John’s face hardened as his eyes narrowed at Dean, but he didn’t confirm or deny Dean’s revelation, which spoke volumes. 

“I mean it, boys,” John growled. Dean huffed and reluctantly nodded his head, but Sam wasn’t so submissive, he never had been to John. 

“I think she can decide for herself who she fucks,” he argued. “Maybe she doesn’t want to have sex with her father, ever thought about that?” Sam pressed. John just glared at Sam, staring him down in hopes of submitting, but Sam held eye contact and refused to budge. 

“Sammy’s got a point, Dad,” Dean spoke up, to Sam’s surprise. 

“Regardless, I want you to promise me you won’t,” John pressed on. Sam looked at Dean and huffed.

“Fine, if you promise me that you won’t take what she’s not giving you,” Sam retorted. John looked almost insulted that Sam would even suggest he could do such a thing, and Sam almost felt bad, but grit his teeth and waited for John’s confirmation anyway. 

“Of course,” John finally nodded. “Don’t you worry about her.” Sam bit his tongue, hating that now there were two men to be jealous of.


	3. Part Three

**Notes for the Chapter:**

> Part Tags: angst, grooming/manipulation, mild father/daughter incest, orgasms, shame, embarrassment, fluff, fake dating, fingering, handjob, voyeurism, mutual masturbation, oral sex (fem rec)

**_Your POV_ **

  
  


You were surprised to see your father's truck pulling up outside the school. You weren't sure which of the three men you'd have rathered. First there was Dean, the brother you'd let finger you this morning, that had cum on the very hand you were clutching to the strap of your school bag with. Then there was Sam, the brother that had confused the fuck out of you on the drive to school that morning with his comments about Dean, and how only  _ maybe  _ incest was wrong, suggesting  _ maybe  _ it wasn't. And then there was your father, the man who you were fairly confident knew what you and Dean had done that morning, the man that you were petrified of letting down or disobeying because you were such a Daddy's girl, and seeing his face as he no doubt talked to you about the absolutely disgusting thing you and his eldest son had done that morning was the last thing you wanted. So as you climbed into his truck and avoided eye contact, you decided that John definitely was the short straw.

“Hey baby girl, good day?” he asked cheerfully. You were thrown off by his tone.

“Yeah, it was okay,” you mumbled.

  
  


The truck rumbled as John pulled off and you started to head back towards the motel. The elephant in the room wanted to rear its ugly head, and you were close to saying something yourself, just to get it over with, when he finally spoke up.

“We should talk about this morning,” John said softly.

“Daddy, I am so sorry, I don't know... I don't know why I did that,” you told him immediately. John hushed you, reaching for your hand in your lap and squeezing it.

“Like I told you, sweetheart, I'd rather it be us than anyone else,” he told you softly. He brought your knuckles to his mouth and kissed them.

“I know but, you weren't serious, they're my brothers,” you reasoned. John glanced across at you.

“It's okay, it's not a big deal,” he reassured you. “You're both adults, you both wanted to,” John pointed out. “You're not hurting anyone.”

  
  


You thought on your father's words. Was it really no big deal? He was right about one thing, you had wanted to.

“You're not mad?” you checked.

“No, baby,” John reassured you, his hand resting on your thigh again. “Dean and Sam are good boys, I know I raised them to treat you well, they adore you like I do,” he smiled, squeezing your leg gently. You bit your bottom lip and nodded, feeling the heat start to pool in your core at his large hand engulfing your thigh. Maybe he was right, maybe it wasn't a big deal, and maybe it was okay for you to feel like this about them – you couldn't help it, after all. “You can mess around with them, but when you feel ready to have sex, I want you to come to me,” he explained. You looked across at him, watching his hazel eyes fix to the road, and you traced the handsome features of his face. What did he mean by,  _ come to him?  _ Was he implying he wanted to be your first? You thought about it for a moment – the idea of losing your virginity to your own father, and after the initial pulse of arousal, you felt disgust, just like you'd done with Dean that morning. You were an awful person for even considering it for a second, of course that wouldn't be what he meant. He probably just wanted you to go to him so he could talk you out of it.

  
  


“Promise me, princess?” he prompted, looking over at you. You nodded your head softly.

“I'm ready now,” you told him. John chuckled to himself, his hand slipping a little higher and you let it, feeling the buzz of his skin against yours, feeling the wetness start to soak into your panties again.

“You think you're ready, sweetheart, but you're not, not yet. But you will be soon.” You wanted to argue with him, and it was like he could read your mind because he quickly added, “Daddy knows best. And when have I ever been wrong, hey?” he smirked. His thumb brushed back and forth along your thigh just like Sam's had done that morning. You wanted him to touch you  _ there,  _ just like Dean had done. But it was wrong and you knew it.

“Are you sure it's okay... what I did with Dean?” you asked timidly.

“Trust me, sweetheart, it's okay. Why would Daddy lie to you, hm?” he pressed. “Like I keep telling you, us three are the only men you can trust, especially me,” he smiled, his fingers digging in slightly.

“I know it should be wrong, but it feels too good,” you admitted. John chuckled.

“Of course it does, sweetheart, because we're special to you.”

“I started it with Dean this morning,” you confessed more confidently now, getting it off your chest, “and I think about Sammy too... and you.” John smirked, and the look of pride on his face only made you feel good about yourself. “I had a naughty dream about you last night,” you went on. “The three of you, you were... going to take my virginity.”

  
  


John's hand slipped a little higher, now completely under the skirt of your dress as his fingers dug in harder, making you clench for a second.

“That what you want, Princess? You want Daddy to take your virginity?” he prompted. You swallowed, the low growl of his voice was only turning you on more and more. You shut up the voice in your head that kept telling you this wasn't right, because the way John's darkened glare was on you, the way he gripped your thigh, only felt good.

“Ye-yes,” you confessed, breathing out heavily, as if the confession had been a weight on your chest.

“I tell you what, baby girl,” John smirked, “why don't we make a deal?” You bit your bottom lip and waited on baited breath for him to continue. “Why don't you let your brothers teach you some stuff, and then when you get good at it, you come and show Daddy what you've learned. And if you're good enough, I'll take your virginity for you, how does that sound?” You whimpered at the very thought, and nodded your head. “Will you do that for me? Save that special first time just for me? No one would make it more special than your Daddy. Make sure my little girl gets the best first time possible.”

You stayed quiet but bit your lip and nodded your head in agreement. 

“What did Dean teach you this morning, Princess?” he prompted. Biting your lip, you hesitated for a moment, before quickly grabbing his hand, and before you could change your mind, you guided it towards your pussy, opening your legs slightly and letting him feel for himself how wet your panties were.

“Hm, someone’s wet just thinking about it,” he purred. You swallowed hard, feeling the heat of his fingers soak through the cotton of your panties. You pressed his fingers harder against you and started to buck your hips, whimpering softly as you looked over at him and bit your bottom lip. Pulling your panties to one side, you let John feel your bare pussy for himself. He growled lowly, and you realised he was driving past the turning for the motel, carrying along down the highway.

“Dean taught me that I like two fingers,” you told him seductively, guiding two of his fingers towards your opening. John hesitated, and then pulled back, returning to rubbing your clit instead.

“Fuck, Princess, you're fucking dripping, I'm about to crash this damn truck.” You wanted him to give in, pull over and fuck you in the back seat. You didn't want to wait any longer. But before you could voice your desires, it was too late, the coil deep inside you snapped and you came hard, John still rubbing at your clit as he slowed and eventually stopped.

  
  


You panted in the passenger seat, and felt the twinge of guilt wash over you, as John finally pulled over at the side of the road.

“You okay, baby?” he asked softly. You nodded quietly. That was twice you'd cum today alone at the hands of one of the men in your family. It was all a bit much. John leaned over and kissed your lips. Not the way he kissed you when you were young, but the way Evan kissed you, with tongue and opened mouths and nibbling of lips. It felt different to Evan, but it felt good and washed away your fears. “Let's get you home, why don't we go out for dinner? Your choice where,” John smiled. You beamed at him and nodded your head. “That's my girl.”

-

Things with Dean hadn't felt so awkward since you'd gotten your father's approval, and even things with Sam weren't all that bad. You sat between them on the sofa, watching Scooby Doo – a firm favourite from your childhood that seemed to always be playing at this time of day. You had one leg hooked over Sam's as you leaned against Dean. You wondered if John would tell them about what had happened between you in the car ride back from school earlier on, as there never seemed to be any secrets in this family - at least the men didn't keep any, you felt you were left out of a lot of loops being the youngest  _ and  _ a female. Dad's cell phone ringing grabbed your attention as you looked over the back of the couch to see him answer it and leave the room.

“I'm starving,” you complained.

“Pizza?” Dean offered.

“Dad said we're going out for dinner – my pick,” you boasted with a smug grin.

“What did you do to deserve that?” Dean grunted. You blushed immediately, thinking about exactly what you'd done, and you noticed Sam scowling at the TV.

“Don't worry, Sammy, I'll pick somewhere we all like,” you reassured him. He looked over at you and offered you a small smile, reaching to squeeze your leg and rub his thumb back and forth a little.

  
  


John came back into the motel room flustered, grabbing some stuff and his jacket.

“Gotta head out for a few days, got a case,” he explained.

“We can come,” you offered, sitting up straight.

“No, you've got school,” he grunted over at you, not even looking in your direction. “Look after her, boys,” he told them both.

“What about me?” Dean offered.

“No, you stay here too, I'll call you if I need you,” John told him. Dean nodded his understanding.

“Daddy,” you pouted.

“It's only gonna be a few days, Y/N, just a vamps nest, but I owe a friend one,” he told you, finally looking at you.

“Okay,” you agreed reluctantly. John smiled at the three of you one last time and then left. As soon as the door was closed you slumped back.

“So, dinner?” Dean asked, trying to keep his tone light.

  
  


You sulked. You'd been looking forward to the meal out as a family like John had promised.

“I'm not hungry, I'm gonna go to bed,” you told them both, getting up. You made your way over to your bed and pushed your skirt off, climbing under the covers in nothing but your panties and your shirt. As usual you lay with your back to the boys and the TV, and stared at the wall until you felt the mattress dip behind you. Dean's arm wrapped around you and he pressed himself close behind you, kissing the back of your shoulder. Dean knew how much you hated when John called off plans or broke promises, and you knew it wasn't John's fault as such, but it still hurt.

“Hey, you want a brother sandwich?” You could feel Dean's smirk as it pressed against the back of your shoulder. “C'mon, it used to cheer you up,” he teased.

“Yeah, when I was like six,” you argued.

“Hey, Sammy? Get over here,” Dean shouted. Sam climbed onto the bed in front of you and slid up tight against you until he was sandwiching you between him and Dean. You giggled at how close the both of them were and tried to get more comfortable.

“Nuh huh,” Dean warned, holding you still, “don't wriggle, that got you into trouble last time,” he laughed. You bit your lip, tempted to keep going, but you hadn't lied when you'd told Dean you were tired, and one glance at Sam told you it would be inappropriate to start something now.

  
  


Looking up at Sam through your lashes you watched him push some hair out of your face, and then his hand traced down your jaw and he tipped your head back. Dean kissed the back of your neck again and you were surprised to feel Sam lean down and kiss your lips, softly and almost hesitantly at first, but when you began to kiss back, Sam deepened it.

“Why don't you show Sammy what I taught you today?” Dean asked. You bit your bottom lip as you pulled back.

“I'm tired,” you told them both. This morning you'd never even made it to second base, the thought of doing that with three different men – family members no less - in one day was daunting. But they didn't know about John. “Tomorrow?” you added. Sam kissed your nose.

“Tomorrow,” he confirmed, “goodnight, sweetheart.”

  
  


-

  
  


The next two days were a bit of a mind numbing blur as you all waited for news from John. You went to school, you came back, watched TV, ate pizza and went to bed. Things seemed to be back to normal with your brothers. Dean hadn't made a pass, Sam hadn't tried to kiss you again. You would be lying if you said you were feeling a little disappointed about the fact. It had gone from too much to not enough overnight. You'd started to mope around, and Dean had picked up on it.

“Hey, why don't we take you to that dinner Dad promised? I've got a new credit card,” Dean offered, as you sat and watched a  _ Friends  _ rerun.

“I'm not up to it, but you two go,” Sam told you both flatly. Come to think of it, Sam had been off too, you'd just been too busy being miserable to notice before now.

“What do you say, sweetheart? Me and you, any place you want,” Dean tempted with a smirk. You giggled and nodded your head.

“Okay, sure,” you agreed. “Let me get changed.”

  
  


You dug in your bag for the dress you'd worn a few days ago, it was the nicest thing you owned that was still  _ you,  _ and changed in the bathroom. Dean was spraying some more aftershave when you stepped out.

“Look at you dressed all pretty,” he smiled. Sam glanced over you and then looked back to the TV without saying a word. “Well, don't wait up for us, Sammy,” Dean winked, “c'mon, sweetheart.” You giggled at Dean's high spirits, and left Sam to mope by himself.

  
  


At the slightly fancier than normal diner you'd chosen, you stood and waited to be seated.

“Howdy love birds, table for two?” The waitress smiled widely at them. Before you could open your mouth and correct her, Dean flung his arm over your shoulder and he pulled you in closer.

“Please,” he grinned back. He continued to walk with you under his arm all the way to the table that she'd selected. “We're celebrating, aren't we, baby?” Dean turned to you as he helped you into your seat like a true gentleman.

“Yeah,” you replied weakly. The waitress  _ Chloe  _ only seemed to smile wider.

“Well celebrating gets you free pie,” she winked.

“Perfect,” Dean beamed. Chloe handed you menus and promised to be back soon. “Free pie,” Dean winked at you. You scoffed and shook your head, looking down at your menu.

  
  


“Look at this, our first date,” Dean sighed.

“I'm your sister,” you reminded him with a smirk.

“And yet I've done things to you no other man has ever done before,” he told you quietly. Your cheeks instantly burned. Dean still didn't know about John, and the longer it went on, the more nervous you were to tell him. But he didn't need to know, did he? 

“So, I think we're past dating,” you replied, clearing your throat and focusing very hard on the menu. You were trying to joke along with him, but your throat was closing up and your mouth felt dry. You could really do with a drink right about now – preferably alcoholic.

“So we're going steady, got it,” Dean teased. You looked up at him and shook your head, rolling your eyes at his playfulness. You placed your menu down and glanced around you.

“You don't actually feel bad about it at all, do you?” you asked, almost in disbelief, “about what we've done?”

  
  


Dean looked at you for a moment and scoffed.

“Oh sweetheart, I've done worse than finger a girl,” Dean laughed.

“Your sister,” you corrected quietly. He held your eye contact.

“I've done worse,” he repeated.

“Like what?” you couldn't help but ask. Dean glanced around and drew a deep breath, placing his own menu down now.

“Let's just say that you're not the only one that needed help with some firsts,” Dean explained.

“Sam?” you blurted out. Dean raised his eyebrows and then looked back at his menu. “Does Dad know?” you checked.

“Yep, told us not to tell you so keep your mouth shut,” he told you, the most brotherly he'd sounded all night.

  
  


You'd never considered either of your brothers to be even attracted to men. Sam's comments in the car that morning suddenly made sense, how he’d had two  _ firsts,  _ how it was different with someone special. He was really talking from experience, he wanted you to have what Dean had given him. You really looked up to Sam and Dean – idolised them, even, so the idea that they'd done all this stuff together before put you at ease somewhat.

“What about Dad?”

“What about him?” Dean pressed.

“Is he... did he get involved?”

“Hell no, not with us,” Dean crinkled his nose, like the idea was disgusting and you felt a shame wash over you. “You're his little girl, it's different with you,” Dean added. Suddenly the disgust turned to pride. You were  _ special,  _ more so than Sam and Dean in some ways, and the thought made you smile.

  
  


-

  
  


Soft rock music played over the speaker as Dean drove you back to the motel in the darkness. Dean had really laid on thick that you were a couple celebrating, because as you were leaving the restaurant he was holding you and even kissed you, making your head spin. You knew it was all fake, but it was still nice to have a  _ date,  _ and it was even nicer to know you trusted the guy you were with more than anything. Maybe they were right – it was different this way.

“I think I need more practise,” you blurted out, biting your lip after the words had left your mouth. Dean glanced across at you and smirked.

“Yeah?” he pressed. You nodded, still biting your bottom lip. Dean's eyes glanced back at the road. “We're almost back,” he noted.

  
  


As you stepped into the motel room it was dark, Sam was already asleep in bed, and Dean closed the door quietly behind him. He pressed his finger to his lips to indicate you were quiet and shoved you back against the wall. You stayed pressed to it even when Dean let you go and bent at the knees to reach under your dress and rip your panties down your legs. He stood back up to full height and spread his arm across the top of your chest, keeping you in place. Your breathing was heavy and irregular as Dean's other hand reached under your skirt and spread your legs wider. His fingers curled through your slick, and he plunged two inside immediately. The stretch burned a little and you whimpered. Dean's arm left your chest and his hand was instantly over your mouth to silence you. But your pussy was making obscene squelching noises around his fingers, you were so aroused. Your legs shook as you struggled to stay standing, and Dean started to curl his fingers, fucking them in and out of you just as perfectly as he'd done the first time. He looked down your body and watched himself work, as you glanced over his shoulder towards Sam. Sam was slowly turning over to face you.

  
  


Dean hadn't noticed, and if he had it didn't stop him, and Sam's eyes opened to look at you. You whimpered again, and Dean's hand pressed harder against your mouth. Sam wasn't looking away, in fact, he kept his eyes fixed to you until you were cumming hard and thick around Dean's fingers, and your legs were giving way. Dean guided you over to the bed next to Sam's and sat down on the edge, thumbing his jeans open and pulling his throbbing cock out. As you glanced back at Sam his eyes were closed again.

“Remember what I taught you?” Dean asked in a whisper. You nodded, lowering to your knees and reaching to wrap your hand around his cock. You tightened your grip a little and started to move your hand up and down slowly, judging Dean's reaction the whole time. “Fuck sweetheart, thought you said you needed practise? You seem pretty damn perfect to me.”

  
  


-

  
  


You were abruptly awoken a few hours later to the sound of Dean's cell phone ringing, and realised when you opened your eyes it was still the middle of the night.

“Yeah?” Dean grumbled, his arm slipping from around you. “Yes, sir.” You knew immediately that it was your father, and Dean slipped out of bed and yawned, fumbling around for his clothes. The bottom of his shirt would've had cum on it, but Dean seemed to pay that no mind as he dressed in it anyway. You sat up, and Dean leaned over the bed to kiss you.

“Go back to sleep, baby, Sammy's still here,” he told you softly, kissing you again. “I'll see you in a couple days, yeah?” he pressed. You nodded silently and watched him leave. You'd always hated the way them going on hunts without you made you feel. You sighed, the bed suddenly feeling far too big, and climbed out of it, tiptoeing over to Sam's bed. Peeling back the covers you climbed in and Sam welcomed you with open arms as he lay there, still half asleep. You curled up against his chest and felt him kiss your forehead, and managed to fall asleep that way until morning.

When you opened your eyes again it was light, and you were still in Sam's arms. You felt yourself relax a little knowing it was a weekend so you didn't have school for two days now. Then you remembered that Dean and your father were away on a hunt, and you turned around in Sam's arms to reach for your cell, to see if they'd checked in yet. Nothing. You checked Sam's next but nothing there either. It made you uneasy not knowing what was going on, and if they were okay or not. You grabbed your cell again and scrolled to Dean's name, before dialling. You waited what felt like forever, and eventually you were sent to voicemail. Chewing your bottom lip anxiously, you decided to try again. The same thing happened for a second time, so instead you tried John. He would pick up if he could. He tried to never miss a call from you. Not that you thought Dean might either. 

When John didn't answer either you started to worry. What if something had happened? Your heartbeat was increasing as you text Dean and asked if he was okay, you couldn't think what else to do. Sitting up completely now, you worried your bottom lip and stared at your cell and waited. 

"Hey sweetheart, what's wrong?" Sam asked as he noticed you awake. You didn't take your eyes off of the cell phone in your lap, the silver flip phone was a stark contrast to the navy and orange patterned bed spread. 

"Dean and Daddy aren't answering," you told Sam nervously. 

"They're probably fine, baby, just busy with the hunt," Sam reassured you. 

"Dad said it was vamps, it's light out," you continued to worry. 

"Baby, sh sh, it's okay," Sam soothed, reaching up to cup the side of your face. You stared at him, and let a small smile creep to your lips as his thumb brushed back and forth lovingly across your cheek. "They're fine. They're probably busy or sleeping it off. We'll hear from them soon." You nodded your understanding and bit your bottom lip. Sam smiled softly and his thumb reached out to tug your bottom lip free from your teeth. "Want me to take your mind off of it?" he asked softly. 

Your heart beat sped up slightly, you and Sam had never done anything more than kiss, even though, dare you admit it, you wanted to. And you knew he did too. Maybe that's why he had been off with you. The last time anything almost happened you'd turned him down. Well, you didn't want to turn him down this time. You wanted to know if he was as good as John and Dean at making you feel good. You had no doubt he was. You nodded your head in his hold and he smirked softly before leaning in and kissing you. You immediately kissed back, deepening the kiss by opening your mouth and gliding your tongue along his. Sam guided you to lay back down, and shifted so he was over you, holding himself up above you as he continued to kiss you passionately. 

Dean occasionally kissed you, but never like this. And John had kissed you in his truck that day, but it didn't last this long. Sam's kisses trailed long your jaw to your neck, and he breathed against your cheek before pressing his mouth to your ear. 

"Wanna show you something new," he breathed. You nodded your head, more than eager to learn more. You'd tried to take it further with Dean the night before, but he was insistent on keeping things at second base. Was he saving third for Sam? "Anyone tasted you before?" Sam asked before biting softly on your neck. You moaned and arched your back into him.

"N-no," you stammered out. The very thought of Sam eating you out made your panties soaked in seconds. Sam's tongue ran up your neck and his teeth caught your earlobe. 

"Good," he growled. His hands went under the hem of your night shirt, and he pushed it up your body, cupping your bare breasts under the cotton. His thumbs rolled over your hardening nipples as he pulled his knees under him so he was kneeling between your opened legs. He bunched your shirt up just above your breasts and sat back on his heels to admire your body that was almost completely bare for him. 

You hooked your fingers into your own panties and pushed them down your legs, unhooking them from your feet and dropping them to the floor beside the bed. Sam's eyes were darker than you'd ever seen them, and he growled a little at the sight of you before him. 

"Fuck baby, you're perfect." You blushed at Sam's statement and smoothed your hand down your own body as you started to slowly swirl your fingers around your bundle of nerves, feeling just how aroused you were for your brother. 

"Fuck Sammy, I'm so wet for you," you whimpered. Sam's large hand smoothed up the inside of your thigh, and the other pawed at the front of his boxers, his cock noticeably hard behind the fabric as he watched you pleasing yourself. 

"Dean teach you how to touch yourself like that, baby? Or did you learn that all by yourself?" You bit your lip and looked up at him with lust blown eyes. The way he was looking at you wasn't just a huge turn on, but a huge confidence boost too. 

"This is how I've always touched myself when I thought about my big brothers. But Dean taught me that I prefer it when someone else is touching me," you hinted seductively. Sam's hand left your thigh, and he playfully slapped your hand away, replacing it with his own as he began to rub in circles over and over, making you arch your back and moan. Sam leaned down and kissed you again, swallowing the uncontrollable gasps and groans that were leaving your mouth. 

Sam's kisses became more feverish, hungry and needy as he kissed down your neck again and over your breasts, stopping to suck your nipple into his mouth. And then his lips moved down and down and down again, until he was shifting to lay on his front between your legs. He encouraged you to hook your legs over his arms and his hands wrapped around to your front to pin your hips to the bed. 

"Bet you taste fucking delicious, sweetheart," Sam growled, his eyes not leaving your pussy, and you'd never felt so exposed. No one had ever been that close before. No one had ever seen you so intimately. Sam turned his head and kissed up your thigh slowly, and you whimpered and writhed beneath him, desperate for friction. 

"P-please Sammy," you stammered, bucking your hips up towards him. You were desperate to feel his mouth there, you'd driven yourself crazy thinking about what it would be like and you were so close to finally finding out. Your fingers combed through the back of his hair as you tried to guide him closer and he nipped at the skin on your inner thigh with his teeth playfully. You grunted, frustrated and Sam smirked against your skin. He kissed the spot just above your clit and his hazel eyes - lust blown and half lidded - looked right at you as he lowered his mouth to your centre, and his tongue licked one stripe from your opening up to your clit. 

Your whole body shuddered in response and your eyes fluttered closed. Sam hummed in approval and lapped again in the same manner, flattening his tongue when he was at the opening but then using the tip at the clit. 

“Holy shit,” you gasped, breath catching in your throat. 

“You taste so fucking good,” he growled, his fingers digging into your hips. He held you still as he closed his lips around your bundle of nerves, sucking it into his mouth and flicking the tip of his tongue over it again. You screamed out, hips bucking up despite his hold, and your thighs clamped closed around his head. Sam continued his assault, licking and sucking and nibbling until you were squirming so uncomfortably beneath him, all you could think about was the orgasm you were about to have on his face. You gripped the back of his head hard, not wanting him to let up for anything, and Sam pressed his face closer to you, lapping harder and not slowing down until you were falling apart around him, thighs quivering, breathing stuttered as you rode out your high against his mouth. 

Sam hummed and licked slowly at your entrance. 

“Fuck, sweetheart, that was hot as fuck, I don’t wanna come up,” he chuckled, placing a slick covered kiss to your thigh. 

“Fuck,” you panted, your mind was spinning. You thought Dean and John had given you good orgasms, but the high you were feeling after having someone’s mouth down there was like nothing you’d ever experienced before. “I am more than happy with you staying down there.”

Sam chuckled, “okay good, because I’m not done with you yet.” And then he started his assault once more. 


	4. Part Four (FIN)

**Notes for the Chapter:**

> Part Tags: blowjob (first time giving), angst, fluff, fake relationship, possessive!Dean, first time, loss of virginity, fingering, oral sex, protected sex, p in v, mentions of wincest (m/m)

Thankfully, Sam was holding your thighs up and apart, because you didn’t have the strength to do that anymore. They were shaking in his hold as he made you cum _yet again._ Your mind was foggy with nothing but post orgasmic bliss, and your body shuddered with every breath you took. Sam placed a kiss to your lower stomach and sat back on his heels, letting your legs go gently as you let them fall back down to the bed and stared at him, panting hard. He had a smug grin on his face that he had every right to wear, as he reached up and wiped his lips clean. 

“You okay there?” he chuckled. You could barely even nod as he moved to lay down next to you again. You could see he was still painfully hard behind his boxers, but he seemed to be ignoring it as he wrapped an arm around you and encouraged you to lay your head on his chest. Looking down his body, you let your fingers trace over his muscles and then a little further down towards the unmissable bulge. 

“You don’t have to, sweetheart,” Sam told you gently as you toyed with the elastic of his boxers. 

“Yeah I do,” you told him, pressing a kiss to his peck. “It’s the least I can do to say thank you,” you smirked, pushing your fingers under his boxers. Much like your other brother, Sam was warm and velvet soft. However, he wasn’t as thick as Dean, but from what you could tell he was longer. Sam reached under your chin to tip your face up and look at him as he kissed you again. You could taste something different on his tongue and assumed it was the remnants of your arousal. You wrapped your hand around him and started to work him the way Dean seemed to like it. Sam groaned softly into your mouth, and delicately wrapped a hand around your throat to hold you there. 

  
  


“Fuck, baby, Dean was right, you’re good at that,” Sam gasped. You smirked, feeling proud. You pushed up, slipping out of his embrace and sat alongside him. Sam’s fingertips brushed along your back softly as you moved his boxers down and pulled his cock out fully. You continued to work him in your hand, feeling far more confident after Sam’s comment, and bit your lip. 

“I wanna taste it,” you confessed. Sam looked up at you, eyes even more lust blown than before. 

“Are you sure?” he asked softly. You nodded your head instantly. 

“Please? Can I try it?” you pleaded. Dean had been hesitant about this part, but Sam just swallowed hard.  
“You don’t have to beg me, sweetheart,” he scoffed. You instantly smiled wide, and moved so your face was closer to his crotch. 

“I’ve - I’ve not done this before,” you reminded him with a blush, suddenly feeling nervous. 

“You’ll be fine, baby,” he reassured you, reaching up and gathering your hair in a fist at the back of your head. “Just take it slow.” You nodded your understanding and opened your mouth, guiding the tip of his cock towards it, and closing around him slowly. You started to suck and swirl your tongue around. There was a tang of something salty, but the warm spongy tip against your tongue felt surprisingly nice. You looked up at him to judge his reaction, watching as his eyes fluttered closed.

“Shit,” Sam gasped, his mouth falling open. You felt confident enough to take a little more, feeling him start to fill your mouth, and you pushed down until he pressed at the back of your throat and made you gag. You instantly withdrew a little. “Careful, baby,” he chuckled, looking back down at you. “Fuck, you’re so hot with my cock in your mouth.” He gasped for air again, and started to slowly thrust up into your mouth. You began sucking again, swirling your tongue as best as you could, and bobbed your head the way they did in the pornos Dean used to let you watch. You reached up and wrapped a hand around the base of his cock and twisted your hand, bringing it up to meet your lips with each thrust. “Holy-” Sam moaned louder. You pulled back.

  
  


“Is it okay?” you asked, worried. 

“Don’t stop, baby,” he begged. “It’s perfect, I’m close already.” You smirked and lowered your mouth again, returning to the rhythm you’d found. Your spare hand reached to cup his balls softly, something else you’d seen them do in porn, and Sam’s fist tightened around your hair as he bucked his hips up a little more forcefully. Spit was starting to dribble down your chin, but you were afraid to stop because Sam seemed to be enjoying it so much. His thighs tensed and he pushed himself as deep as he could get. You were prepared this time, and managed to control the gag when he nudged the very back of your throat, and felt him cum. It was warm, more of that salty taste like to begin with, as you swallowed it down and pulled back. 

  
  


Sam was panting hard, head thrown back and he slowly relaxed, looking down at you as you reached up and dried your mouth on the back of your hand. His hand let go of your hair and smoothed down your back again. 

“Are you okay?” he asked.

“Yeah, are you?” you chuckled. You’d never seen Sam quite so out of sorts. He gave you a drunk looking smile and nodded his head. 

“Best I’ve had, I’m not just saying that,” Sam said, looking at you. 

“Really? That was my first time,” you reminded him. 

“Really, baby,” he nodded. 

“Dean’s gonna be pissed,” you smirked. Sam frowned a little, but a smirk came to his lips. 

“Why? Because I gave you your first? He had plenty of chance,” Sam scoffed. 

“No, because I’ve outdone him,” you teased. 

  
  


Sam’s eyes widened, he’d clearly not been aware that you knew about him and Dean. 

“I’m not gonna let him forget it.” You chuckled to yourself as you climbed out of bed and heard Sam laugh along too. “I’m gonna shower,” you told him. 

“Mind if I join you?” he asked. 

“Absolutely not,” you smirked. 

  
  


  
  


Seeing John’s truck and the Impala in the motel parking lot made you smile as you returned from breakfast with Sam at the diner down the road. 

“They’re back!” you exclaimed, already jogging to the motel room. Sam didn’t seem to share the same enthusiasm you did about their return, but you didn’t care. You swung the door open and saw Dean unpacking some stuff on the bed, and then your father was sitting at the dining table. 

“You didn’t return my calls,” you told them, instantly heading over to your father. You climbed into his lap and buried your face into his neck. 

“Careful, baby girl,” John grunted and when you pulled back you saw the bandage on his shoulder. 

“What happened?” you asked immediately.

“I’m fine, just a scratch.” John smiled at you warmly, and you were so happy that he was okay you kissed his lips without even thinking about it. You pulled back and cleared your throat. 

  
  


You turned to Dean and smiled at him. 

“I was worried about you,” you told him, getting up off John’s lap and approaching him, before wrapping your arms around his middle. Dean dropped what was in his hand and hugged you back, kissing your hairline. 

“Me? You had nothing to worry about, sweetheart,” he laughed. 

“Yeah well, you weren’t answering your cells, and after Dad called you away in the middle of the night… ” you explained. Sam came into the room and said hi to them both.  
“Where are we going?” he suddenly asked. You kept your arms around Dean’s waist but turned your head to see he was packing, not unpacking like you originally thought. 

“Time to move on, Sammy,” John explained. You sighed. It was something you should be used to now, but it never got easier starting a new school. Luckily, you didn’t have long left before you could hunt full time with them. 

  
  


“You got anyone you wanna say goodbye to, sweetheart?” Dean asked you. 

“Well given that Evan hasn’t talked to me since the day he met you two, no,” you told him, standing back and crossing your arms over your chest. 

“Good, you’re ours,” Sam commented. You looked over at him and blushed, them being possessive of you had a whole new meaning now, and it only made you more aroused. Dean looked between the two of you and started to smirk, but didn’t comment. 

“I’m gonna load the truck,” Dad announced, leaving you alone with your brothers.

“How was third base?” Dean smirked, looking between the two of you. 

“How did you know?” you asked. Dean tilted his head to the side and cocked an eyebrow. “I’m better than you,” you boasted with a smug grin. Dean looked over at Sam immediately, and Sam just offered a shrug with a smirk. “Best he’s ever had apparently.” There was nothing quite like sibling rivalry, and you barely ever got anything up on either of your brothers. You were going to savor this. 

“Sammy!” John called in and Sam sighed, leaving you alone with Dean now. You looked back at Dean and smirked again. 

  
  


“Well, guess I’ll have to find out for myself what all the fuss is about, hey?” Dean murmured, reaching up to drag his thumb along your bottom lip. 

“Guess you will,” you whispered. “So you wanna do that stuff now, huh?” you pressed. Dean smirked and shrugged. 

“Had to let Sammy have one of the firsts,” Dean told you, folding another pair of jeans and putting them in his bag. You took your cue to start packing your own things in your bag. “As Dad wants the biggest first of all,” he added, carefully. He glanced over at you. 

“Yeah,” you nodded. 

“If that’s what you want,” Dean said. You blushed. It was still weird to you to be admitting it out loud, especially to your brother, but it was getting more and more _normal_ already. No wonder Dean and Sam didn’t bat an eyelid about that stuff anymore, they’d been doing this much longer than you.

“Yeah, I do, it would be special,” you agreed. Dean nodded along and closed his bag. 

“Not gonna pretend I’m not jealous, but maybe after your first time…” 

“Yeah, I’d like that,” you nodded. “Sam too,” you added. 

  
  


Dean looked at you for a moment and scoffed. 

“Sam too, that would be hot,” he admitted. He walked over to you, his bag slung over his shoulder and grabbed the back of your neck to kiss you. “I think you should ride up front with me,” he smirked against your lips. “Would love to feel that pretty little mouth around my cock as I drive.” You bit your bottom lip at the very thought. Dean stepped back and headed for the door. “You’ll have to call shotgun before Sammy, though, or it’ll be his mouth I’ll be fucking.” He shot a wink at you before heading outside. Part of you debated taking your time, the idea of seeing your brothers together was admittedly quite the turn on. 

_**Two Weeks Later** _

  
  


Your new school was worse than the last one, full of judgmental assholes who had a thousand questions for you. You’d made up some cock and bull story about living in a motel whilst your new family home was being renovated, not wanting them to know that you’d never had one of those before. On your third day, Dean dropped you off in the Impala and made a point of kissing you goodbye - on the lips and very passionately. You were mortified, worried that they’d find out he was your brother, but he laughed it off and told you to tell people that he was your boyfriend, which you happily did once all the questions came in about him. The girls gushed over him, and the guys made sly, jealous comments about him. But at least none of them hit on you – you assumed that had been Dean’s aim the whole time. Now, not only were you the talk of the school for being the new kid, but you were the talk of the school for having an older boyfriend that drove a cool old car and was _super hot._

  
  


Everyone automatically assumed that you were having sex with him, and asked a million inappropriate questions whenever they got talking to you. You figured you weren’t gonna be sticking in this town long, John was already talking about moving further north next month, so you lied through your teeth, made up elaborate stories, and tried to join in with all the sex conversations during lunch times. But it wouldn’t be long until the lies caught up with you, you’d already almost been caught out a couple of times, having to stop yourself from saying _my brother, Dean_ and pretending you only had one brother, Sam. Each day that Dean picked you up he’d lean against the hood of the Impala, hands deep in his leather jacket and wait for you, smiling and kissing you hello as you approached. You didn’t mind people seeing that once they all assumed he was your boyfriend. For once, you were somewhat popular.

  
  


It was strange to get back to the motel and have to remind yourself that Dean _wasn’t_ your boyfriend, in fact, he was your brother. But that didn’t stop you from dry humping, or sucking him off on the car rides back to the motel, or letting him finger you under the blanket when you watched a movie. And it certainly didn’t stop Sam sharing showers with you, going down on you when John and Dean would go off to do the smaller, simpler hunts. Dean and Sam both shared a bed with you now, leaving John with his own double on the nights he was actually around. And even when he wasn’t, you’d usually end up in the same bed, Dean fingering you, grinding his erection into you from behind, whilst you wanked Sam off on the other side. You were starting to gain quite the experience between the two of them. Nothing had happened with John since, no matter how hard you’d tried to flirt and get him to give in whenever he’d send Sam and Dean on a supply run together.

  
  


“You have had actual sex with Dean, right?” Ruth asked with her eyebrows raised skeptically.

“Yeah, of course,” you scoffed, brushing her off.

“What’s your favourite position?” she pried. You bit your lip and thought about it.

“I like being on top,” you told her. Technically only half a lie – when you and Dean dry humped, you enjoyed being on top then. Ruth seemed to buy it as she continued to talk about how her and her boyfriend, Dylan, had tried having sex in the shower on the weekend, and you shut off from the conversation, drinking some juice as you grabbed your cell out.

  
  


_**< I’m ready** _

_**> Are you sure?** _

_**< Yeah, been getting lots of practice like you said. Please? ** _

_**> I’ll pick you up after school and we can talk about it.** _

The rest of the school day seemed to drag, but eventually you were heading towards your father’s truck, listening to your new friends complain that Dean wasn’t picking you up, so they couldn’t stare at him, though Emily did make a comment that your father was attractive too. You pretended to be disgusted by the idea, but you weren’t. As you climbed into the truck you were itching to kiss him, but settled for kissing his cheek, knowing there were eyes on you.

“Good day, sweetheart?” he asked.

“Yeah,” you smiled, grabbing your seatbelt and plugging it in. You let the silence grow, but not for long, too eager to get the conversation started. “So my text,” you prompted.

“Ah yes,” John sighed, as if he hadn’t been thinking about it – even though he no doubt had.

“I am ready, Daddy,” you told him. “I’ve been practicing, I’m really confident with it all now,” you smiled. John glanced across at you and looked at your face for a moment.

“I spoke to your brothers, and they agree, they think you’re ready,” he nodded.

“Great,” you beamed.

“I’m gonna ask you one last time, are you sure this is what you want… with me?” he pressed.

“If it wasn’t you I’d want it to be Sam or Dean,” you told him honestly. You didn’t know any other guy anywhere near well enough, and you didn’t want to wait to find one either.

  
  


John stayed quiet for a moment and you wondered if he was finally going to give in to you.

“Open the glove box,” he commanded softly, nodding at it. You reached forward and opened it, coming face to face with a gun, moving it to one side you found what you assumed he wanted you to. There was a motel key and a box. Pulling the box out you realised it was condoms. You blushed a little, and realised that John was judging your reaction.

“Gotta be sensible,” you noted with a smirk.

“That’s right,” John nodded. You looked down at the motel key, realising that it wasn’t the room number you’d been staying in.

“Got us our own room for the night,” he explained, “I thought… we could be completely alone, it would be more special that way.”

“Okay,” you agreed, feeling the nerves in your stomach. This was becoming real. But you weren’t second guessing it. Looking across at John, you only felt the arousal pool between your legs. You were finally going to have sex, and not just with anyone.

  
  


You carefully placed the condoms and key back in the glove compartment and closed the door again. John seemed a little confused by you returning them for a second, until you turned to the side and unbuckled your seat belt slowly.

“What’re you doing?” he asked slowly, watching you intently. You bit your bottom lip and reached over to his crotch, rubbing your hand over where he was starting to get hard.

“I always thank Dean for picking me up from school, thought I’d thank you too,” you purred.

“Jesus, sweetheart. I don’t wanna crash the damn truck, be patient,” he scolded. But his fight was weak, he didn’t once reach down to physically stop you, so you continued to rub over the growing bulge.

  
  


“You feel longer than Sam,” you commented, “thicker than Dean too,” you added. A strangled groan bled through his lips. “Hope you fit. Did they tell you how tight I am?”

“Jesus Christ, where did you learn to speak that filth?” John grunted. “You’ve been spending too much time with Dean and those damn pornos, huh?” he prompted. You giggled and bit your bottom lip.

“Maybe,” you teased, your fingers playing with the zipper of his jeans.

  
  


John kept glancing down at your hand then back at the road.

“I’m serious, baby girl, need you to wait. We’re almost there.” His tone was more forceful than before, so you decided to obey him, reluctantly slipping your hand away and returning it to your lap.

“Fine, doesn’t mean I can’t play,” you told him, pushing your hand into your own jeans.

“When did I raise such a bad little slut?” John growled.

“Don’t you like me being naughty, Daddy?” you asked him innocently.

“Fuck, I love it.” You giggled at his confirmation, and noticed the sign for the motel. You slipped your hand back out, and tried to seem somewhat composed as you parked up. You grabbed the key and the condoms, putting them in your pocket, and got out of the car. John’s hand dug into his pocket as he grunted, and then you started to walk. The Impala was parked outside your usual room, but John led you a few doors down to the new room.

  
  


The new room only had one double bed in it, and there were already beers on the dining table. John didn’t let you drink often, and as soon as you clocked them he warned you that you were only allowed one. He didn’t want you under the influence. He wanted you to remember it all. You placed the condoms down alongside the beers and shrugged your jacket off, throwing it over the back of the chair. You were suddenly less confident than you’d been in the car. It was all so real now. You chewed your bottom lip as John grabbed you a bottle of beer and twisted off the cap before handing it to you. You took several swigs to wet your dry mouth.

“We don’t have to, not today,” John reassured you.

“I want to, Daddy, please,” you told him sweetly. He took a swig of his own beer, before placing it down on the side and stepping forward. You did the same with your beer, and let him pull you into him before feeling his lips on yours. This was just like any time with Sam and Dean. Lord knows there had been countless times you’d wished they’d taken it further, wished you didn’t have to end it where you always did, and at least this time you wouldn’t be.

  
  


“Daddy’s got you baby, it’s gonna be so good,” John soothed. You nodded in agreement as you reached up and started to unbutton his plaid shirt. You pushed it over his shoulders, and he let it drop to the floor, before kissing you a little more passionately. He undid your shirt and cupped your breasts in your white lace bra. You started to undo his jeans, now a pro at opening them with one hand without looking. He wasn’t wearing underwear, so as you pushed the jeans down his legs, his cock sprang free fully hard. You wrapped your hand around it and whimpered. He’d felt bigger than your brothers, but this was confirmation. He was about as long as Sam, but he was as thick as Dean too – a lethal combination.

“Gonna show me what you’ve learned, baby?” he prompted. You nodded and slowly lowered to your knees at his feet. You looked up at him through your lashes as you gripped his cock and moved your hand up and down his length slowly, twisting left and right just slightly every time. John groaned, his cock hardening still as it twitched in your hand. You leaned forward and tapped the tip on your tongue, looking up at him through your lashes before taking him a little deeper and a little deeper until he was all the way at the back of your throat. You’d gotten used to this now, knowing your limits and only choking when you allowed yourself to. You had learned that Sam liked them more sloppy, more rough than Dean, and you considered what your father would like. Sam and John were more alike than they cared to admit, it was why they butted heads so often, so you decided to try it Sammy’s way, sucking harder and bobbing your head a little faster, and John groaned loudly and thrust his hips forward. 

“Fuck, baby, you been getting plenty of practice, or are you just a natural?” you smirked up at him and kissed the tip of his cock. John reached down and pulled you back to your feet. “Lay on the bed,” he instructed. You did as you were told, watching as John stepped out of his jeans on his way over to the bed. You’d never seen your father totally naked. Fuck, you needed him. 

  
  


You reached to unbutton your own jeans and started to push them down your legs. 

“You’re unwrapping my present,” John teased, watching you with his cock in his fist. You chuckled as you kicked your jeans off and reached for your panties. “Nuh huh, those are mine,” John growled. Biting your lip, you nodded your agreement. John climbed over you and kissed you passionately again. 

  
  


You were growing desperate. Desperate to be touched, desperate to feel him inside you. Just _desperate._ Your touch had to be telling him that, as your hands became restless, gripping his biceps then reaching for his cock. 

“Calm down, sweetheart. Relax. Daddy’s got you,” he soothed. You giggled slightly, a blush burning your cheeks. John reached between your legs and started to rub over the crotch of your panties, humming as you began to whimper. “That’s it baby. Feel good?” he asked. You nodded your head eagerly, biting your bottom lip. John moved his hand inside your panties and continued to rub, his fingers sliding down to your opening with complete ease thanks to your arousal. “So fucking wet for your daddy. I’m gonna slide right in,” he purred. He nudged two fingers at your entrance and they easily slid inside. Your body had been used to taking that by now, Dean had even managed three a couple of times. 

  
  


John groaned at the feeling of your pussy wrapped around his fingers, and started to fuck them in and out of you slowly, scissoring them to stretch you open and prepare you. His thumb rubbed at your clit as he worked, and you moaned, bucking your hips and grinding them down harder onto his fingers. John pulled back, leaving you moaning desperately for more, and hooked his fingers into your panties, pulling them down your legs and throwing them to the floor. 

“Touch yourself, baby,” he ordered softly. Your hand flew to between your legs as you immediately obliged and started to rub at your clit. John walked over to the dining table, took a swig of beer, and then grabbed the box of condoms. He tore into the packaging, getting one out, and made his way back over to you quickly. He dropped to his knees at the foot of the bed, and pulled your body closer to the edge, spreading your legs wide. His beard scratched at the delicate skin on the insides of your thighs as he lowered his mouth to your sex. He started to lap at your juices, sucking on your clit and nipping it between his teeth. 

“Fuck, Daddy,” you whined, resting back on your elbows and looking down your body to watch him. 

  
  


John got you to the very edge with his mouth, to the point you were clamping your thighs around his head and begging him to keep going when he finally pulled back. Your cunt was throbbing, the orgasm tingling at your skin, not quite at the surface enough for you to let go. John climbed back to his feet, and you noticed he’d already put the condom on, kneeling down between your legs as he gripped the base of his cock and lined himself up with your opening. 

“Deep breaths for me baby, this might hurt a little,” he warned you. He nudged the head in first, which burned a little but it was bearable, and then he dared another couple of inches, and another, and then he sank the rest inside until he was fully seated. You were breathless, no words forming on your tongue even if you wanted them to. 

“Fuck,” you whispered, barely audible. 

  
  


“Jesus, you’re tight,” John groaned, reaching between your legs and rubbing at your clit. “Look at that baby, Daddy’s all the way in, not my innocent little girl anymore.” You bit your bottom lip and shook your head, watching as he slowly withdrew and slid back inside again, over and over. The pressure was like nothing you’d ever felt, but you liked it. It was better than fingers or a mouth. It was perfect. You fisted at the bedsheets, feeling the burn as you stretched around him and your body got used to the new intrusion, and John continued to rub your clit, which helped you relax. The orgasm he’d denied you was back, threatening to come out again, and as John picked up the speed and you felt his cock nudge all the sweet spots inside you, you came undone, clenching around him and stopping him in his tracks. 

  
  


“Fuck baby girl, that pussy feels too good, making Daddy wanna cum already,” he gasped. “Feel good?” he checked. 

“Yes, yes, Daddy, don’t stop,” you begged, rolling your hips to encourage him to fuck you again. John smirked at your confirmation and started to fuck you once more, a little harder and faster for every minute that passed, until it was a speed and strength you assumed he’d normally use. You lay there, groping at your chest as he fucked you and moaned loudly, chanting _Daddy_ and telling him how good he felt on repeat. John’s blunt fingernails dug into the side of your thigh until he leaned over you completely and kissed you, holding his forehead to yours. 

“Gonna cum, baby, your little pussy is gonna make Daddy cum,” he grunted. 

“Yes, Daddy, please, cum inside your little girl,” you begged. John’s eyes fluttered closed as his hips stuttered and he pushed himself impossibly deeper, so much so it was almost painful. 

  
  


When John finally pulled out and discarded the condom, he pulled you into him and encouraged you to lay with him on the bed. Your eyes were so heavy, your body so completely satisfied, that you fell asleep on his chest almost instantly. 

When morning came around, your body ached, but the scratch John had itched was back, and you wondered if it would ever go away completely. You wanted more, couldn’t think about anything else but being fucked over and over again by John and Sam and Dean. You didn’t want to go to school, you wanted to show your brothers what you were now capable of, wanted to feel them inside you, wondering if they’d feel different. You wanted to try different positions, you wanted to try different styles. Rough and nasty, slow and sweet - you wanted it all, and you wanted it with the three men that cared for you more than anything. 

  
  


When you finally got back to your normal room to get your stuff for school, Sam and Dean were still in bed, both in the same one and the spare double bed still made. 

“There she is, our little sister is no longer a girl but a woman,” Dean smirked as soon as you stepped through the door. “How was it?” John hadn’t followed you in, so you closed the door behind you and bit back a wide smile. 

“It was really good,” you gushed. Both the brothers looked pleased for you, and you climbed onto the bed, squeezing between them. “Thank you, both of you, for making sure my first times were all special,” you blushed. Both your brothers turned on their sides to face you.

“Told you, sweetheart, no one will ever do it like us,” Dean boasted. 

  
  


“So what’s next?” Sam asked. You bit your bottom lip. 

“Think Dad will finally let me take birth control now?” you asked. Dean chuckled. “But in terms of firsts… I don’t know.” 

“Anal,” Dean smirked. 

“What?! No, no way,” you argued. Sam laughed, smoothing his hand over your stomach. 

“It’s not that bad, feels pretty good, actually,” Dean shrugged. You smirked at him and bit your bottom lip. 

“Hm, that’s an idea for my next first,” you purred, rubbing your hand down Dean’s front, under the covers, and you were pleasantly surprised to find he was naked and starting to get hard. “A threesome, you can fuck me whilst Sam fucks you.” Sam hummed in approval behind you and Dean bit back a smirk. 

“Well, I think that would be a first for all of us, but I’m game if you are.” You looked back over your shoulder at Sam and he smirked down at you. 

“I can’t wait,” he replied, kissing you softly as Dean kissed your neck.


End file.
